MiMeDB: Showing metabocard for Dimethylsulfide (MMDBc0000215)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:40:04 UTC

Update Date

2022-08-31 00:14:56 UTC

Metabolite ID

MMDBc0000215

Metabolite Identification

Common Name

Dimethylsulfide

Description

Dimethylsulfide is the predominant volatile sulfur compound (VSC) in breadth malodor, a metabolite of suplatast tosilate (a dimethylsulphonium compound for the treatment of asthma) in patients that regularly take that medication. (PMID 14628896 ). Dimethylsulfide is a sulfur containing organic chemical compound with a disagreeable odor. In vapor form it is produced by cooking of certain vegetables, notably corn and cabbage, and seafood. It is also an indication of bacterial infection in malt production and brewing. It is a breakdown product of dimethylsulfoniopropionate, and is also produced by the bacterial metabolism of methanethiol. Dimethylsulfide in concentrated liquid form is insoluble and a flammable (Wikipedia ). This is a microbial metabolite that can be found in Bradyrhizobium, Cyanothece, Escherichia, Pseudomonas and Rhizobiaceae (PMID: 25807229 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
(METHYLsulfanyl)methane	ChEBI
2-Thiapropane	ChEBI
[SMe2]	ChEBI
Dimethyl sulphide	ChEBI
DMS	ChEBI
Methyl sulfide	ChEBI
Methyl thioether	ChEBI
(METHYLsulphanyl)methane	Generator
Dimethyl sulfide	Generator
Methyl sulphide	Generator
Dimethylsulphide	Generator
Dimethyl sulfoxide(reduced)	HMDB
Methylthiomethane	HMDB
2-Thiopropane	HMDB
Dimethyl monosulfide	HMDB
Dimethyl sulfide (natural)	HMDB
Dimethyl thioether	HMDB
Dimethylsulfid	HMDB
Methanethiomethane	HMDB
Methyl monosulfide	HMDB
Methylthiomethyl radical	HMDB
MSM	HMDB
Reduced-dmso	HMDB
Thiobis-methane	HMDB
Thiopropane	HMDB

Molecular Formula

C₂H₆S

Average Mass

62.134

Monoisotopic Mass

62.019020882

IUPAC Name

(methylsulfanyl)methane

Traditional Name

dimethyl sulfide

CAS Registry Number

75-18-3

SMILES

CSC

InChI Identifier

InChI=1S/C2H6S/c1-3-2/h1-2H3

InChI Key

QMMFVYPAHWMCMS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dialkylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two alkyl groups.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thioethers

Sub Class

Dialkylthioethers

Direct Parent

Dialkylthioethers

Alternative Parents

Substituents

Dialkylthioether
Sulfenyl compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aliphatic sulfide (CHEBI:17437 )
an organosulfur compound (CPD-7670 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	18.5 g/L	ALOGPS
logP	0.59	ALOGPS
logP	1.22	ChemAxon
logS	-0.53	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	18.89 m³·mol⁻¹	ChemAxon
Polarizability	7.24 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01ot-9000000000-8ed5810ef2a492b40ae1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01ot-9000000000-aab0fb854ed08a99a142	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01ot-9000000000-b8e506cefc1462c55765	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01ot-9000000000-8ed5810ef2a492b40ae1	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01ot-9000000000-aab0fb854ed08a99a142	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01ot-9000000000-b8e506cefc1462c55765	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dj-9000000000-452048d3bfa7a40636c4	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-01ot-9000000000-8ed5810ef2a492b40ae1	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-01ot-9000000000-360d47e40fcfcf205bf3	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-01ot-9000000000-b8e506cefc1462c55765	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9000000000-ae1ff184cb043d43cd3a	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9000000000-189f32d3eb2bb107bad1	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-5579d822eaf64cbda3b3	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-9000000000-45a7990a4b612cb72664	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-9000000000-3bb7835f1011f708503e	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ox-9000000000-d5b5c0545e3e2ec5e98e	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-9000000000-6fc9e9a3cbf6090ab8d5	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9000000000-6fc9e9a3cbf6090ab8d5	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-9000000000-6fc9e9a3cbf6090ab8d5	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9000000000-f865abc3930f083f5ea2	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9000000000-f865abc3930f083f5ea2	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-efaeb46b008ef59dd3de	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01ot-9000000000-3da3b740e54dd0695ac8	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, cyclohexane, experimental)		2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		2015-03-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Adipose Tissue
Blood
Cerebrospinal Fluid (CSF)
Feces
Intestine
Kidney
Liver

Tissue Locations

Adipose Tissue
Intestine
Kidney
Liver

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192081	Indolethylamine N-methyltransferase	Unknown	O95050	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0007751	Dimethyl sulfoxide	Dimethylsulfide	Not Available	Dimethyl sulfoxide reductase (Menaquinol 8)	VMH	30371894
MMDBr0007752	2-Demethylmenaquinol 8	2-Demethylmenaquinone 8	Not Available	Dimethyl sulfoxide reductase (Demethylmenaquinol 8)	VMH	30371894
MMDBr0008025	Dimethyl sulfoxide	Dimethylsulfide	Not Available	Dimethyl sulfoxide reductase (Menaquinol)	VMH	30371894
MMDBr0008026	2-Demethylmenaquinol 8	2-Demethylmenaquinone 8	Not Available	Dimethyl sulfoxide reductase (2-demethylmenaquinone)	VMH	30371894
MMDBr0013937	S,S-dimethyl-beta-propiothetin	Acrylate	Putative dimethylsulfonioproprionate lyase DddL	Non-hydrolytic bond cleavage (or its reversal)	RHEA	34755880
MMDBr0014979	Dimethylsulfide	Dimethyl sulfoxide	Dimethylsulfide dehydrogenase subunit alpha	Dehydrogenation	RHEA	34755880
MMDBr0015039	Dimethylsulfide	Formaldehyde	Dimethyl-sulfide monooxygenase	Oxygenation	RHEA	34755880
MMDBr0016514	Methanethiol	Dimethylsulfide	Methanethiol S-methyltransferase	Methylation	RHEA	34755880
MMDBr0024838	Water	Dimethyl sulfoxide	Putative dimethyl sulfoxide reductase catalytic subunit A	Reduction	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Dimethyl sulfide poisoning		Association	Human Blood	HMDB	1874893

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Archaea	Euryarchaeota	1		Microbial culture
Bacteria	Proteobacteria	88	Pig ; Human feces; Human stool; Human ; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria	Actinobacteria	17	Human feces; Human ; Human nasopharyngeal swab; Human supragingival plaque	Metabolic reconstruction
Bacteria	Firmicutes	14	Human feces; Human	Metabolic reconstruction
Bacteria/NULL	Proteobacteria	2	Pig ; Human feces; Human stool; Human ; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria	Cyanobacteria	1
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Stem	Brassica oleracea var. gongylodes	FooDB	31437929
Plant	Plant	Solanum tuberosum	FooDB	31437929
Plant	Fruit	Rubus	FooDB	31437929
Plant		Apium graveolens var. dulce	FooDB	31437929
Plant	Bulb	Allium sativum l. var. sativum	FooDB	31437929
Plant		Brassica oleracea var. italica	FooDB	31437929
Plant	Leaves		FooDB	31437929
Plant	Leaves		FooDB	31437929
Plant	Plant	Allium schoenoprasum	FooDB	31437929
Plant	Leaves	Petroselinum crispum	FooDB	31437929
Plant		Apium graveolens var. rapaceum	FooDB	31437929
Plant	Leaves		FooDB	31437929
Plant	Fruit	Rubus	FooDB	31437929
Plant	Essential oil	Allium cepa	FooDB	31437929
Plant	Essential oil	Mentha spicata	FooDB	31437929
Plant	Leaves	Camellia sinensis	FooDB	31437929
Plant	Oil	Allium cepa	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	3224.8	403.1			uM	Adult (>18 years old)	Male	Dimethyl sulfide poisoning	HMDB	1874893
Human Cerebrospinal fluid (csf)	Detected and Quantified			0	1	uM	Adult (>18 years old)	Both	Normal	HMDB	15996001
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Campylobacter jejuni infection	HMDB	17314143
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Clostridium difficile infection	HMDB	17314143
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	17314143
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Ulcerative Colitis	HMDB	17314143
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	19167006
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	21494609
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	HMDB	23454028
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	23454028
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Crohn's disease	HMDB	24811995
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24811995
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Ulcerative colitis	HMDB	24811995
Human Feces	Detected and Quantified	343.344				nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	HMDB	26416813
Human Feces	Detected and Quantified	563.299				nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	HMDB	26416813
Human Feces	Detected and Quantified	649.135				nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	HMDB	26416813
Human Blood	Detected and Quantified	3224.8	403.1			uM	Adult (>18 years old)	Male	Dimethyl sulfide poisoning	HMDB	1874893
Human Feces	Detected and Quantified	343.344				nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	HMDB	26416813
Human Feces	Detected and Quantified	563.299				nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	HMDB	26416813
Human Feces	Detected and Quantified	649.135				nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	HMDB	26416813
Human Cerebrospinal fluid (csf)	Detected and Quantified			0	1.0	uM	Adult (>18 years old)	Both	Normal	HMDB	15996001
Human Adipose tissue	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	17314143
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	19167006
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	23454028
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24811995
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	21494609

External Links

HMDB ID

HMDB0002303

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Dimethyl_sulfide

METLIN ID

6603

PubChem Compound

1068

PDB ID

Not Available

ChEBI ID

17437

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Terazawa K, Kaji H, Akabane H, Takatori T: Determination of dimethyl sulphide in blood and adipose tissue by headspace gas analysis. J Chromatogr. 1991 Apr 19;565(1-2):453-6. doi: 10.1016/0378-4347(91)80409-6. [PubMed:1874893 ]
Gahl WA, Ingelfinger J, Mohan P, Bernardini I, Hyman PE, Tangerman A: Intravenous cysteamine therapy for nephropathic cystinosis. Pediatr Res. 1995 Oct;38(4):579-84. doi: 10.1203/00006450-199510000-00018. [PubMed:8559613 ]
Yeung CK, Lang DH, Thummel KE, Rettie AE: Immunoquantitation of FMO1 in human liver, kidney, and intestine. Drug Metab Dispos. 2000 Sep;28(9):1107-11. [PubMed:10950857 ]
Rosen RT, Hiserodt RD, Fukuda EK, Ruiz RJ, Zhou Z, Lech J, Rosen SL, Hartman TG: The determination of metabolites of garlic preparations in breath and human plasma. Biofactors. 2000;13(1-4):241-9. doi: 10.1002/biof.5520130137. [PubMed:11237188 ]
Jiang T, Suarez FL, Levitt MD, Nelson SE, Ziegler EE: Gas production by feces of infants. J Pediatr Gastroenterol Nutr. 2001 May;32(5):534-41. doi: 10.1097/00005176-200105000-00009. [PubMed:11429513 ]
Murata T, Fujiyama Y, Yamaga T, Miyazaki H: Breath malodor in an asthmatic patient caused by side-effects of medication: a case report and review of the literature. Oral Dis. 2003 Sep;9(5):273-6. doi: 10.1034/j.1601-0825.2003.02874.x. [PubMed:14628896 ]
Engelke UF, Tangerman A, Willemsen MA, Moskau D, Loss S, Mudd SH, Wevers RA: Dimethyl sulfone in human cerebrospinal fluid and blood plasma confirmed by one-dimensional (1)H and two-dimensional (1)H-(13)C NMR. NMR Biomed. 2005 Aug;18(5):331-6. doi: 10.1002/nbm.966. [PubMed:15996001 ]
Carrion O, Curson ARJ, Kumaresan D, Fu Y, Lang AS, Mercade E, Todd JD: A novel pathway producing dimethylsulphide in bacteria is widespread in soil environments. Nat Commun. 2015 Mar 25;6:6579. doi: 10.1038/ncomms7579. [PubMed:25807229 ]

Showing metabocard for Dimethylsulfide (MMDBc0000215)

MOL for #<Metabolite:0x00007fe2d6818678>

3D MOL for #<Metabolite:0x00007fe2d6818678>

3D SDF for #<Metabolite:0x00007fe2d6818678>

3D-SDF for #<Metabolite:0x00007fe2d6818678>

PDB for #<Metabolite:0x00007fe2d6818678>

3D PDB for #<Metabolite:0x00007fe2d6818678>

SMILES for #<Metabolite:0x00007fe2d6818678>

INCHI for #<Metabolite:0x00007fe2d6818678>

Structure for #<Metabolite:0x00007fe2d6818678>

3D Structure for #<Metabolite:0x00007fe2d6818678>